Blind Date
by LeafxGreenx3
Summary: "Why're you here out of all places?"... "I saw you sitting alone and figured that you've probably gone through enough suffering by sitting here alone so I decided to ease it and join you." When May agrees to tag along with Leaf on her date with Gary, she has no idea what she has coming for her. Contest, Oldrival. For SunshineTails!


**Once again, I've reached another hundred, so congratulations SunshineTails! I'm hoping you'll enjoy this, despite the fact that I haven't written a Contestshipping fic in a looooong time. Hopefully I haven't lost my touch yet, ha, ha. **

**Disclaimer: I own nothing. **

**~(:**

**Blind Date**

"No, I'm not going to go on this date with you and Gary," a brunette rejected, her arms crossed under her chest.

Another brunette clapped her two hands together and pouted. Her hazel eyes filled with innocence. "Come on, May, please?" she begged.

"Why don't you just ask Dawn or Misty to tag along with your date with Gary, Leaf?" May inquired.

Leaf only rolled her eyes. "I can't ask them because Ash and Misty are visiting his mom back at Pallet Town and Dawn and Paul already made plans for tonight. Please, May, it's our first date and things can get awkward."

"It's going to be even more awkward when I'm there!" she retorted, catching attention from the people in the café they were in.

The two girls laughed nervously before quieting down again. "Please, May? Do it for me, your best friend. Plus, you can get your own separate table to watch us from afar! If we get quiet, just call me and give me a topic. And Gary can get Drew to go too!"

May shook her head immediately at the mention of the green haired teen. "No way am I going to go along if he's going."

Leaf only rolled her eyes. "But it would be like a double date, which will make things so much less awkward." With that, she pulled her one and only puppy-dog look and the brunette didn't buy it at first, only because she was immune to it.

When Leaf saw that the brunette wasn't going to buy it, she pouted even more and sniffed her fake tears away, causing May to look and few bad instantly and sighed out of frustration. "Fine," she finally said, making Leaf cheer. "But, if you two start getting all lovey-dovey then I'm leaving. And don't invite Drew," she added. "He annoys me."

Leaf just ran up and hugged her friend happily. "You're the best person ever. And for that, I'll treat you to another item on the menu!"

The sapphire-eyed girl giggled and faked a thinking pose. "Well, since it _is _your treat, then I'll have another slice of chocolate cake."

Leaf only nodded as she stood up to walk to the cashier to order another cake. "Coming right up," she chimed cheerfully.

So for the next half hour, the two girls stayed in the café, talking and laughing. When they were done, the left and walked down the streets of La Rousse City, going back to Leaf's house to get ready for her date.

"I don't get it," May wondered aloud as she sat back on a beanbag in Leaf's room as the other brunette looked through her closet. "Gary's like the biggest flirt ever, why would things get awkward between you two. Besides, you two clicked like when you first met."

Leaf laid a strapless striped green dress on her bed and looked at May. "That's because he told me that I'm the first girl that he was ever serious about, so that means that he'll do his best to make this night like really good, so it may be awkward and all, you know?"

May sighed as she thought about it. Leaf did have a point. Gary Oak was never really serious about any other girl but Leaf. "Where is he taking you to anyway?"

"He's taking _us _to a fancy restaurant. He never gave me the name though," she answered as she dropped a pair of white flats next to her dress. "Come on, May, pick a dress to wear."

"Why do I have to wear one too? I'm not the one on a date," she retorted as she looked ever her nails.

Leaf puffed out her cheeks as she grabbed a coral one-strap dress from her closet before making her way to May and dropping it on her lap. "If you don't wear it, you'll stick out. And this dress is as casual as it can get, so wear it, please?"

May examined the dress as she thought about her answer. It wasn't red, her favorite color, but the coral was a nice color too. She looked up from the dress and Leaf's brown eyes were pulled into its innocent puppy-dog face. This caused the brunette to sigh. "Okay, fine, I'll wear it." She fiddled with the waist tie as Leaf went back to her closet to look for shoes. "Where did you get this dress anyway? I've never seen you wear it before."

The brunette came back with a pair of strappy gladiator sandals with a flat point one heel. "It was a Christmas gift from my aunt. If you like it, you can have it. The color doesn't really go with me."

"Wow, thanks." Then she stood up. "Well then, let's get you ready for your date now."

~(:

It was seven when the girls were done preparing and just in time as well because they heard the doorbell go off. "Hey, where are your parents?" May inquired as they made their way to the door.

"They're off on a business trip and won't be back until tomorrow," she answered casually. When she reached the door, she opened it and smiled at the person who was on the other side. "Hey there," she greeted.

The person returned the smile before handing her a bouquet of flowers. "Hey yourself," he replied before kissing her on the cheek. Then he saw May next to Leaf. "Hey, May."

She greeted him back with a nod. "So Leaf told me that I'll be tagging along and that I'll be getting my own table."

Gary only looked at the girl next to him in confusion as she grinned up at him. "It's to ease up on the possible awkwardness," she admitted.

"So that's why you asked me to reserve another table." She only nodded back in response and with that, they were off.

~(:

"They seem to be getting along perfectly well," May murmured to herself as she watched from a few tables away. She took another bite from her salad as she texted Dawn and Misty.

From a few tables away, Leaf smirked as she saw May slowly draw her attention from her and Gary. "So when is he coming?"

The brunet in front of her looked at his phone and smirked back. "He should be here soon." The two chuckled at the thought of May's face. "Are you sure she's not going to kill you for this?"

"Of course I'm sure. Besides, they're bound to get together anyway, so why not now?"

Back at May's table, the brunette's plate of steak finally arrived and she happily ate, drawing her attention away from the two couple. Then someone stood arrived to her table, who May assumed was the waiter until she heard a familiar chuckle.

"If you're trying to catch a guy's attention, it's not going to help by eating like that," he remarked.

The brunette's sapphire eyes narrowed to a glare at him before sticking a tongue out at him. "Why are you here?" As she asked that question, he took a seat across from her. "And why're you sitting in front of me?"

"I'm going to have dinner," he answered simply before flicking his bangs from his eyes. "Waiter, I need a menu," he called to the nearest waiter.

The brunette only looked at him. "What are you doing? If you want dinner, then get your own table."

He closed the menu and looked at the brunette in front of him, taking in her beauty before smirking. "Now why would I do that when there's an open chair? Besides, have you seen the waiting line?" The same waiter came up to him, notepad in hand. "I'll have the Grilled Chicken sandwich with a glass of iced water. Salad as the side order, thanks."

May only glared at him. "Fine, then you're paying for both our food then since you took over my table."

He only smirked and shrugged. "We'll see how the evening goes then," he joked, causing her to give him a kick to the knee. "Okay, fine, I'll pay sheesh. What're you doing here anyway?"

Her sapphire eyes shifted to the table behind him and he followed her eyes. "Leaf asked me to come with her and Gary because she thought that they were going to be all awkward and all since it was their first date and all."

"They seem to be doing fine," he pointed out.

"I can see that," she deadpanned.

He then turned his attention back to her. "Then why're you still here?"

May only shrugged at the question before taking another bite out of her steak. "I promised her I'd be here and I already had a table and all, so I thought why not. Why're you here out of all places?"

Like May, Drew shrugged. "I saw you sitting alone and figured that you've probably gone through enough suffering by sitting here alone so I decided to ease it and join you," he explained, dodging the kick she sent towards him. He smirked at her. "Nice try," he commented, infuriating her even more.

When his food finally arrived, May was just about done with her food. "Seriously though, why're you here? I thought you only ate homemade food at home."

He took a bite out of his sandwich before answering. "No one's home today," he answered simply. "The chef's out sick today and my parents are working late tonight so I had two choices: cook at home or come out to eat. I couldn't find a place to eat though so when I saw that you were eating alone, I thought why not join and poke some fun in."

At this, she almost blushed. _Almost. _But he didn't need to see that. So now that she knew why he was there, the two decided to converse, getting to know each other better, with Drew's rude comment occasionally. Of course, it wasn't that long since they were friends already but they were able to learn so much more. May was able to learn that it was rare for Drew's parents to be home and that he usually had dinner alone while Drew learned that May only had dinner with her little brother, Max because her parents were always busy with work, just like his. They were so distracted that they didn't even notice Leaf and Gary leaving the place.

"I told you she'd forget about us when he arrives," Leaf teased as she left with her boyfriend.

He only rolled her eyes at her in response before slipping his jacket over her shoulders. "I never doubted you from the beginning.

~(:

"I'm surprised," he said. "You look like someone who enjoys dinner with her family everyday," he remarked.

"And I figured that you were the type who ate alone." She laughed as he playfully glared at her. "I was just kidding, kinda." Then her eyes wandered off to the empty table behind Drew. "Leaf and Gary left already."

Drew turned to look and just shrugged. "Huh, seems like they did."

"So I guess we should start going too," she said as she stood up. "Shoot, Gary was my ride home too."

"I can give you a ride," he offered. Then his lips curved into a smirk. "If you pay for half of the check."

She shook her head at that request. "Did you forget the fact that you stole half my table? You owe me for that."

His emerald green eyes rolled as he went up to pay while she waited. When he returned, he left the tip and the two left together.

"So, when's our next date?" he asked as she was getting out of the car. He flicked his bangs and smirked upon seeing her stop on her tracks and that streak of red on her face.

"W-what are you talking about?" she questioned as she turned to him.

He chuckled slightly and smirked again. _'She can be so cute sometimes when she's confused.'_ "I can't believe you didn't figure it out. Leaf and Gary set the whole thing up as a blind date." When she didn't say anything, he tossed a red rose towards her, which she caught easily since it was a usual thing. "So I'll pick you up at seven tomorrow."

"Whoa, hold on there, buddy. I never agreed to the next date."

Drew just smirked as an idea popped into his head. "Oh right, I completely forgot that you still have to recuperate after spending such an amazing time with the Drew Hayden."

"Oh, you're hilarious," she retorted sarcastically. "And just so you know, you're not amazing at all."

He raised an eyebrow at her. "Oh yeah? Care to prove that theory?"

"Tomorrow, seven, better not be late," she ordered. "Be prepared to discover the fact that you're not amazing at all." And with that, she was out of the car and into the house.

"What did I just get myself into?"

~(:

**Yeah, I'm pretty sure I lost my touch with Contestshipping ): I'm so sorry if you didn't like it, SunshineTails but if you want, I can always delete this and you'll never ever hear from it again and just rewrite another one! It's all up to you though c: **

**For anyone else who had to suffer through this, tell me how much you like it, how much it sucked, and so on. Yeah, my feelings will be hurt but that's what being an author is all about so review please :3**


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